Simon Caulfield: Player–Coach Leadership & Legacy

About this episode

In this episode, Director of Place Kangaroo Point, 𝗦𝗶𝗺𝗼𝗻 𝗖𝗮𝘂𝗹𝗳𝗶𝗲𝗹𝗱 unpacks how he’s built an office where top performers have their own identities—not “from Simon’s office”—and why the business must thrive without him. We get into pathways from 500k GCI to seven figures, case studies across high-volume vs high-value models, and Simon’s personal playbook: two champagne COI events a year, a “favorites” list he calls religiously, and being a present, trusted local over flashy ads. In this Simon shares lessons from moving upmarket (from $555k beginnings to KP’s top end), the difference between selling resi and selling the dream off-the-plan, and the player-coach balance of leading six team presentations a week while still listing and selling. He dives into Wolfpack Fridays, retaining top talent by giving them reasons to stay, using an AI recorder to capture meetings and train staff, and the three-corner support team (manager, coach, trainer). Above all: listen intently, play to your strengths, move the needle each year, and leave people in a better place than you found them. Topics covered: ⚬ Building a business where agents thrive under their own brands ⚬ Leadership mindset: “Leave people in a better place” ⚬ Pathways from 500k to $1M+ GCI and choosing the right model ⚬ Case studies: high-value vs high-volume strategies ⚬ Simon’s COI playbook: champagne events & “diamond” call list ⚬ Moving upmarket: perception, results, and social proof ⚬ Resi vs off-the-plan: selling the dream before it exists ⚬ Player–coach leadership and when to step back from listing ⚬ Wolfpack Fridays: training, collaboration, and shared challenges ⚬ Retaining top talent with support, recognition, and care ⚬ Practical AI for onboarding and process improvement ⚬ Legacy: success measured by impact, not trophies #RealEstatePodcast #SimonCaulfield #RealEstateAgents #RealEstateCoaching #AgentGrowth #Leadership #PlayerCoach #RealEstateSuccess #BusinessGrowth #WolfpackCulture